Deblocking reaction of chemically amplified positive DUV resists.

“…[3,4]. Activation energies for the deprotection reactions of ethoxyethyl, tetrahydropyranyl and BOC units in KrF resists [3][4][5][6] and those for tertiary ester units in ArF resists [7,8] have been reported. However, the relationship between the activation energy and polymer structure was not fully discussed.…”

Section: Introductionmentioning

confidence: 99%

Activation Energies for Deprotection Reaction of Chemically Amplified Resists: A Study Using In-situ FT-IR Spectroscopy.

Shinozuka

Tsunooka

Itani

et al. 2002

J. Photopol. Sci. Technol.

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“…This phenomenon would be consistent with the previous reports of deprotection reaction analysis. 20,21) Film thickness loss of A/G/H and M/G/H resist were investigated after the exposure at 193 nm and PEB treatment from 70 °C for 200 s to 150 °C for 200 s as shown in Fig. 6.…”

Section: Deprotection Reaction Analysis Of Methyl Acetal Resistmentioning

confidence: 99%

Characteristics of low E a 193-nm chemical amplification resists

Ogata¹,

Kinoshita²,

Furuya³

et al. 2006

SPIE Proceedings

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Polymers with methyl acetal ester moiety in the side chain as acid labile protecting group were synthesized and their thermal property, plasma stability and chemical amplification (CA) positive-tone resist characteristics were investigated. 2-Admantyloxymethyl (AdOM) groups in the copolymer indicated lower glass transition temperatures and higher thermal decomposition temperatures than those of 2-methyl-2-admantyl (MAd) groups in the copolymer. AdOM polymer film showed smooth surface roughness after Ar plasma exposure compared with MAd polymer film due to the high thermal stability. The activation energies (E a ) of these deprotection reactions were calculated from Arrhenius plots of these deprotection reaction rate constants. In the low post exposure bake (PEB) temperature region, the E a of these resists decreased in the order MAd > AdOM. The low E a methyl acetal resists displayed good thermal flow resist characteristics for contact holes printing. In addition, the low E a methyl acetal resist achieved a wide exposure latitude of 8.1 % and depth of focus of 400 nm for printing 80 nm 1:1 dense line pattern using NSR-306C (NA 0.78, 2/3 annular). Furthermore, the 65 nm 1:1 dense lines using ASML XT1400 (NA 0.93, C-Quad) for low E a methyl acetal resist pattern showed no tapered and no footing profiles and small roughness on the lines pattern sidewall was observed. 1, INTRODUCTION193 nm lithography including immersion lithography is drawing attention as the successor of optical lithography for the technology nodes of 65 nm, 45 nm, and possibly even beyond 32 nm. 1,2) Therefore, there has been many researches for the base polymer and monomer materials for 193 nm CA positive-tone resists. It is generally known that a suitable protecting group plays an important role in obtaining a good lithographic performance for CA positivetone resist. 3) In our previous work we reported effects of the newly bulky methyl acetal ester as acid labile protecting group on resist characteristics of methacrylate polymers and the relationship between the protecting group structure and deprotection reaction mechanism. 4-6) These results suggest that the newly bulky methyl acetal ester protecting group is effective for further controlling good lithographic performance such as exposure sensitivity, line-edge roughness and PEB sensitivity due to the lower E a compared with tertiary alkyl ester protecting group. However, the relationship between the methyl acetal ester protecting group structure and thermal property of copolymer was not fully discussed. In recent years many papers on low E a CA resist and thermal property of 193 nm CA resists have been reported for the purpose of applying immersion lithography process, thermal flow process and plasma cure process. [7][8][9][10][11] In this paper we report thermal property, plasma stability, deprotection reaction mechanism and high lithographic performance for low E a methyl acetal resist. 2, EXPERIMENT Materials2-Methyl-2-adamantyl methacrylate (M) and γ-butyrolactone-2-yl methacrylate (G) we...

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“…3) We focused on monomers with acid-cleavable protective groups, and we propose some novel monomers. 4) There were various reports about the deprotection reaction of CA positive-tone resists [5][6][7][8][9][10][11][12][13] , because the reactivity of a protective group is a factor affecting resist properties, i.e., sensitivity, dissolution behavior, resolution, and Line width roughness. However, there are few reports focused on the deprotection reactions of monomers with protective groups.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and evaluation of novel resist monomers and copolymers for ArF lithography: Part II

Numata

Fukumoto

Tachibana

et al. 2008

Advances in Resist Materials and Processing Technology XXV

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We synthesized several new monomers with an acid-cleavable protective group and investigated their deprotection reactions. Polymers were prepared using these monomers, and their thermal properties and dissolution rates were investigated. The acidic reactivity of protective groups of these monomers was evaluated using a method we developed. The activation energies [E a (experimental)] calculated using reaction rate constants were found to correlate to some extent with the activation energies [E a (calculated)] calculated from MOPAC. The dissolution rates of some polymers containing similar protective groups as structures were measured. The dissolution rates were related to the polarity and molecular volume (MV) of the decomposed products of protective groups.

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Deblocking reaction of chemically amplified positive DUV resists.

Cited by 5 publications

References 6 publications

Activation Energies for Deprotection Reaction of Chemically Amplified Resists: A Study Using In-situ FT-IR Spectroscopy.

Activation Energies for Deprotection Reaction of Chemically Amplified Resists: A Study Using In-situ FT-IR Spectroscopy.

Characteristics of low E a 193-nm chemical amplification resists

Synthesis and evaluation of novel resist monomers and copolymers for ArF lithography: Part II

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